HCID 67105255, compound → HCID 59557017, compound
Reaction equation
C(OC([NH:11][CH:12]([CH3:25])[C:13](=[O:24])[C:14]([CH2:22][CH3:23])([CH2:20][CH3:21])[C:15](OCC)=[O:16])=O)C1C=CC=CC=1>CO.[C].[Pd]>[CH2:20]([C:14]1([CH2:22][CH3:23])[C:13](=[O:24])[CH:12]([CH3:25])[NH:11][C:15]1=[O:16])[CH3:21]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of ethyl 4-{[benzyloxy)carbonyl]amino}-3-oxopentanoate (3.0 g) in acetone (50 mL) were added potassium carbonate (2.83 g) and iodoethane (2.45 mL), and the mixture was refluxed overnight. After allowing to room temperature, potassium carbonate (2.83 g) and iodoethane (2.45 mL) were added, and the mixture was refluxed for 1 day. After allowing to room temperature, water was added and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=20:1→3:2) to give ethyl 4-{[(benzyloxy)carbonyl]amino}-2,2-diethyl-3-oxopentanoate as a colorless oil (yield: 1.91 g, 53%). To a solution of ethyl 4-{[(benzyloxy)carbonyl]amino}-2,2-diethyl-3-oxopentanoate (1.91 g) in methanol (15 mL) was added 10% palladium carbon (containing 50% water, 1.0 g), and the mixture was stirred under a hydrogen atmosphere overnight. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure to give the title compound as a colorless solid (yield: 920 mg, 99%).
Workup
- filtrationThe reaction mixture was filtered
- concentrationthe filtrate was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-90336e118f4045f89d6aba6cc937282e
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08420694B2
Reaction notes
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